EP3015471B1 - Novel bisalkoxysilane compound and its production method - Google Patents
Novel bisalkoxysilane compound and its production method Download PDFInfo
- Publication number
- EP3015471B1 EP3015471B1 EP15189287.4A EP15189287A EP3015471B1 EP 3015471 B1 EP3015471 B1 EP 3015471B1 EP 15189287 A EP15189287 A EP 15189287A EP 3015471 B1 EP3015471 B1 EP 3015471B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oxy
- bis
- group
- methylamine
- ethylamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- -1 diolefin compound Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 28
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 26
- 150000002430 hydrocarbons Chemical group 0.000 description 26
- 239000000654 additive Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 16
- 230000000996 additive effect Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 125000005370 alkoxysilyl group Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- IMKQQFVOCJNMCT-UHFFFAOYSA-N N-methyl-2-(3-trimethoxysilylpropoxy)-N-[2-(3-trimethoxysilylpropoxy)ethyl]ethanamine Chemical compound CO[Si](OC)(OC)CCCOCCN(C)CCOCCC[Si](OC)(OC)OC IMKQQFVOCJNMCT-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(CN(**)*(C)I)O* Chemical compound CC(CN(**)*(C)I)O* 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDKOACMFBZXJAA-UHFFFAOYSA-N 2-(3-diethoxysilylpropoxy)-N-[2-(3-diethoxysilylpropoxy)propyl]-N-ethylpropan-1-amine Chemical compound CC(CN(CC)CC(C)OCCC[SiH](OCC)OCC)OCCC[SiH](OCC)OCC GDKOACMFBZXJAA-UHFFFAOYSA-N 0.000 description 1
- WYYDEQHNRYSUMH-UHFFFAOYSA-N 2-(3-diethoxysilylpropoxy)-N-[2-(3-diethoxysilylpropoxy)propyl]-N-methylpropan-1-amine Chemical compound CC(CN(C)CC(C)OCCC[SiH](OCC)OCC)OCCC[SiH](OCC)OCC WYYDEQHNRYSUMH-UHFFFAOYSA-N 0.000 description 1
- GUAUKTWJPZIKTO-UHFFFAOYSA-N 2-(3-diethoxysilylpropoxy)-N-[2-(3-diethoxysilylpropoxy)propyl]propan-1-amine Chemical compound CC(CNCC(C)OCCC[SiH](OCC)OCC)OCCC[SiH](OCC)OCC GUAUKTWJPZIKTO-UHFFFAOYSA-N 0.000 description 1
- FMPNQLMWGHAJDG-UHFFFAOYSA-N 2-(3-dimethoxysilylpropoxy)-N-[2-(3-dimethoxysilylpropoxy)propyl]-N-ethylpropan-1-amine Chemical compound CC(CN(CC)CC(C)OCCC[SiH](OC)OC)OCCC[SiH](OC)OC FMPNQLMWGHAJDG-UHFFFAOYSA-N 0.000 description 1
- FUZZDEGKVXOPTB-UHFFFAOYSA-N 2-(3-dimethoxysilylpropoxy)-N-[2-(3-dimethoxysilylpropoxy)propyl]-N-methylpropan-1-amine Chemical compound CC(CN(C)CC(C)OCCC[SiH](OC)OC)OCCC[SiH](OC)OC FUZZDEGKVXOPTB-UHFFFAOYSA-N 0.000 description 1
- HWQJCFFXBXAVCG-UHFFFAOYSA-N 2-(3-dimethoxysilylpropoxy)-N-[2-(3-dimethoxysilylpropoxy)propyl]propan-1-amine Chemical compound CC(CNCC(C)OCCC[SiH](OC)OC)OCCC[SiH](OC)OC HWQJCFFXBXAVCG-UHFFFAOYSA-N 0.000 description 1
- RGQGJJUFFJKKTA-UHFFFAOYSA-N 2-(3-ethoxysilylpropoxy)-N-[2-(3-ethoxysilylpropoxy)-2-methylpropyl]-2-methylpropan-1-amine Chemical compound CC(CNCC(C)(C)OCCC[SiH2]OCC)(OCCC[SiH2]OCC)C RGQGJJUFFJKKTA-UHFFFAOYSA-N 0.000 description 1
- PQLVTXUNPOAFQV-UHFFFAOYSA-N 2-(3-ethoxysilylpropoxy)-N-[2-(3-ethoxysilylpropoxy)-2-methylpropyl]-N,2-dimethylpropan-1-amine Chemical compound CC(CN(C)CC(C)(C)OCCC[SiH2]OCC)(OCCC[SiH2]OCC)C PQLVTXUNPOAFQV-UHFFFAOYSA-N 0.000 description 1
- WNOOQPHLSYOMRN-UHFFFAOYSA-N 2-(3-ethoxysilylpropoxy)-N-[2-(3-ethoxysilylpropoxy)-2-methylpropyl]-N-ethyl-2-methylpropan-1-amine Chemical compound CC(CN(CC)CC(C)(C)OCCC[SiH2]OCC)(OCCC[SiH2]OCC)C WNOOQPHLSYOMRN-UHFFFAOYSA-N 0.000 description 1
- QKTGKWOXSHQZJV-UHFFFAOYSA-N 2-(3-methoxysilylpropoxy)-N-[2-(3-methoxysilylpropoxy)-2-methylpropyl]-2-methylpropan-1-amine Chemical compound CC(CNCC(C)(C)OCCC[SiH2]OC)(OCCC[SiH2]OC)C QKTGKWOXSHQZJV-UHFFFAOYSA-N 0.000 description 1
- GGRFOBYGIWVHRO-UHFFFAOYSA-N 2-(3-methoxysilylpropoxy)-N-[2-(3-methoxysilylpropoxy)-2-methylpropyl]-N,2-dimethylpropan-1-amine Chemical compound CC(CN(C)CC(C)(C)OCCC[SiH2]OC)(OCCC[SiH2]OC)C GGRFOBYGIWVHRO-UHFFFAOYSA-N 0.000 description 1
- YGZNCJNOMBVYLV-UHFFFAOYSA-N 2-(3-triethoxysilylpropoxy)-N-[2-(3-triethoxysilylpropoxy)ethyl]ethanamine Chemical compound C(C)O[Si](OCC)(OCC)CCCOCCNCCOCCC[Si](OCC)(OCC)OCC YGZNCJNOMBVYLV-UHFFFAOYSA-N 0.000 description 1
- DUIVBVCQMSBLSN-UHFFFAOYSA-N 2-(4-diethoxysilylbutoxy)-N-[2-(4-diethoxysilylbutoxy)propyl]-N-ethylpropan-1-amine Chemical compound CC(CN(CC)CC(C)OCCCC[SiH](OCC)OCC)OCCCC[SiH](OCC)OCC DUIVBVCQMSBLSN-UHFFFAOYSA-N 0.000 description 1
- LPIVLPFESCSFFR-UHFFFAOYSA-N 2-(4-diethoxysilylbutoxy)-N-[2-(4-diethoxysilylbutoxy)propyl]-N-methylpropan-1-amine Chemical compound CC(CN(C)CC(C)OCCCC[SiH](OCC)OCC)OCCCC[SiH](OCC)OCC LPIVLPFESCSFFR-UHFFFAOYSA-N 0.000 description 1
- HBLYSLXVTWIXCH-UHFFFAOYSA-N 2-(4-diethoxysilylbutoxy)-N-[2-(4-diethoxysilylbutoxy)propyl]propan-1-amine Chemical compound CC(CNCC(C)OCCCC[SiH](OCC)OCC)OCCCC[SiH](OCC)OCC HBLYSLXVTWIXCH-UHFFFAOYSA-N 0.000 description 1
- WLBAPUFWKACNSI-UHFFFAOYSA-N 2-(4-dimethoxysilylbutoxy)-N-[2-(4-dimethoxysilylbutoxy)propyl]-N-ethylpropan-1-amine Chemical compound CC(CN(CC)CC(C)OCCCC[SiH](OC)OC)OCCCC[SiH](OC)OC WLBAPUFWKACNSI-UHFFFAOYSA-N 0.000 description 1
- HNHSKPJVJPGEQF-UHFFFAOYSA-N 2-(4-dimethoxysilylbutoxy)-N-[2-(4-dimethoxysilylbutoxy)propyl]-N-methylpropan-1-amine Chemical compound CC(CN(C)CC(C)OCCCC[SiH](OC)OC)OCCCC[SiH](OC)OC HNHSKPJVJPGEQF-UHFFFAOYSA-N 0.000 description 1
- WPNZBNHXWCOIAD-UHFFFAOYSA-N 2-(4-dimethoxysilylbutoxy)-N-[2-(4-dimethoxysilylbutoxy)propyl]propan-1-amine Chemical compound CC(CNCC(C)OCCCC[SiH](OC)OC)OCCCC[SiH](OC)OC WPNZBNHXWCOIAD-UHFFFAOYSA-N 0.000 description 1
- YXQQDJUJEUTSQX-UHFFFAOYSA-N 2-(4-ethoxysilylbutoxy)-N-[2-(4-ethoxysilylbutoxy)-2-methylpropyl]-2-methylpropan-1-amine Chemical compound CC(CNCC(C)(C)OCCCC[SiH2]OCC)(OCCCC[SiH2]OCC)C YXQQDJUJEUTSQX-UHFFFAOYSA-N 0.000 description 1
- UCBYXLYJRZTWKY-UHFFFAOYSA-N 2-(4-ethoxysilylbutoxy)-N-[2-(4-ethoxysilylbutoxy)-2-methylpropyl]-N,2-dimethylpropan-1-amine Chemical compound CC(CN(C)CC(C)(C)OCCCC[SiH2]OCC)(OCCCC[SiH2]OCC)C UCBYXLYJRZTWKY-UHFFFAOYSA-N 0.000 description 1
- IMWJVQCNUXDCRV-UHFFFAOYSA-N 2-(4-ethoxysilylbutoxy)-N-[2-(4-ethoxysilylbutoxy)-2-methylpropyl]-N-ethyl-2-methylpropan-1-amine Chemical compound CC(CN(CC)CC(C)(C)OCCCC[SiH2]OCC)(OCCCC[SiH2]OCC)C IMWJVQCNUXDCRV-UHFFFAOYSA-N 0.000 description 1
- RUAFKLZTERZVLI-UHFFFAOYSA-N 2-(4-methoxysilylbutoxy)-N-[2-(4-methoxysilylbutoxy)-2-methylpropyl]-2-methylpropan-1-amine Chemical compound CC(CNCC(C)(C)OCCCC[SiH2]OC)(OCCCC[SiH2]OC)C RUAFKLZTERZVLI-UHFFFAOYSA-N 0.000 description 1
- WOQAYKFIONXXQE-UHFFFAOYSA-N 2-(4-methoxysilylbutoxy)-N-[2-(4-methoxysilylbutoxy)-2-methylpropyl]-N,2-dimethylpropan-1-amine Chemical compound CC(CN(C)CC(C)(C)OCCCC[SiH2]OC)(OCCCC[SiH2]OC)C WOQAYKFIONXXQE-UHFFFAOYSA-N 0.000 description 1
- BWFGLTMOXVURGH-UHFFFAOYSA-N 2-(4-triethoxysilylbutoxy)-N-[2-(4-triethoxysilylbutoxy)ethyl]ethanamine Chemical compound C(C)O[Si](OCC)(OCC)CCCCOCCNCCOCCCC[Si](OCC)(OCC)OCC BWFGLTMOXVURGH-UHFFFAOYSA-N 0.000 description 1
- FLXCEZDXHIODHM-UHFFFAOYSA-N 2-(4-trimethoxysilylbutoxy)-N-[2-(4-trimethoxysilylbutoxy)ethyl]ethanamine Chemical compound CO[Si](OC)(OC)CCCCOCCNCCOCCCC[Si](OC)(OC)OC FLXCEZDXHIODHM-UHFFFAOYSA-N 0.000 description 1
- WYAUJBHSDXYDEE-UHFFFAOYSA-N 2-(5-diethoxysilylpentoxy)-N-[2-(5-diethoxysilylpentoxy)propyl]-N-ethylpropan-1-amine Chemical compound CC(CN(CC)CC(C)OCCCCC[SiH](OCC)OCC)OCCCCC[SiH](OCC)OCC WYAUJBHSDXYDEE-UHFFFAOYSA-N 0.000 description 1
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- WVPMZPPOQHWLGN-UHFFFAOYSA-N 2-(5-dimethoxysilylpentoxy)-N-[2-(5-dimethoxysilylpentoxy)propyl]-N-methylpropan-1-amine Chemical compound CC(CN(C)CC(C)OCCCCC[SiH](OC)OC)OCCCCC[SiH](OC)OC WVPMZPPOQHWLGN-UHFFFAOYSA-N 0.000 description 1
- CQSJVPKFFPHLKT-UHFFFAOYSA-N 2-(5-dimethoxysilylpentoxy)-N-[2-(5-dimethoxysilylpentoxy)propyl]propan-1-amine Chemical compound CC(CNCC(C)OCCCCC[SiH](OC)OC)OCCCCC[SiH](OC)OC CQSJVPKFFPHLKT-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Definitions
- the present invention relates to a bisalkoxysilane compound which is useful as a silane coupling agent, surface treating agent, resin additive, coating additive, adhesive, fiber treating agent, and the like. This invention also relates to its production method.
- Aminosilane compounds are useful for silane coupling agent, surface treating agent, resin additive, coating additive, and adhesive
- aminosilane compounds having hydroxyethyl group are particularly suitable for use in such application due to the high degree of freedom enabled by the presence of a spacer between the amino group and the silyl group.
- Examples of such aminosilane compound having the hydroxyethyl group include dimethylaminoethyloxypropyltrimethoxysilane and dimethylaminoethyloxypropylmethyldimethoxysilane, and these compounds have been described to be useful for use as the silane coupling agent, surface treating agent, resin additive, coating additive, and adhesive (Patent document 1: Korean Patent No. 10-1249352 ).
- Such aminosilane compounds having the hydroxyethyl group also include compounds having carbonyl group, sulfonyl group, carbamoyl group, or oxycarbonyl group on the nitrogen demonstrating the high variety of the aminosilane compounds (Patent document 2: USSN 2003/0196958 ).
- All of these compounds have only one alkoxysilyl moiety per molecule, and sufficient coupling effect may not be realized at the alkoxysilyl group moiety when the compound is used as a silane coupling agent, surface treating agent, resin additive, coating additive, or adhesive.
- N,N-Bis(Trimethysilylpropoxy-ethyl)-aniline is known from Polymer Preprints 2003, 44(1), 125, with CAS registry number 532930-34-0 ;
- JP2010-100544 discloses 3-[3-(diethoxymethylsilyl)propoxy)-N,N-diethyl-2-[(trimethylsilyl)oxy]-1-propanamine and related compounds as coating additives;
- US2003/049486 discloses bis(trialkoxysilylpropyl)amines as coating additives.
- the present invention has been completed in view of the situation as described above, and an object of the present invention is to provide a compound which is capable of exhibiting a higher effect than the compounds as described above when used as a silane coupling agent, coating additive, adhesive, or the like. Another object of the present invention is to provide a method for producing such compound.
- the inventors of the present invention conducted intensive study and found out that a novel bisalkoxysilane compound of the general formula (1) having two alkoxysilyl moieties in the molecule can be obtained by dihydrosilylation of a particular diolefin compound represented by the general formula (2) as described below, and since this bisalkoxysilane compound has two alkoxysilyl moieties in the molecule, the merit of the alkoxysilyl moiety will be fully realized when the compound is used as a coating additive, adhesive, silane coupling agent, or the like.
- the present invention has been completed on the basis of such findings.
- the present invention provides the bisalkoxysilane compound and its production method as described below.
- the bisalkoxysilane compound provided by the present invention has two alkoxysilyl moieties in the molecule, and therefore, when the compound is used as a coating additive, adhesive, silane coupling agent, fiber treating agent, surface treating agent, resin additive, or the like, the merit of the alkoxysilyl moiety will be fully realized. Accordingly, properties of the resulting product will be improved by the addition of the compound, and the use of such compound is useful for such application.
- the bisalkoxysilane compound of the present invention is a compound represented by the following general formula (1): wherein R 1 is a hydrogen atom or an unsubstituted monovalent hydrocarbon group containing 1 to 10 carbon atoms; and R2 is hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group containing 1 to 10 carbon atoms wherein the substituted monovalent hydrocarbon group has a substituent selected from among alkoxy group and a group comprising a halogen atom; R 3 is a straight chain or branched divalent hydrocarbon group containing 3 to 10 carbon atoms, R 4 is a straight chain or branched divalent hydrocarbon group containing 3 to 10 carbon atoms optionally containing a heteroatom, R 5 and R 6 are respectively a monovalent hydrocarbon group containing 1 to 10 carbon atoms, and n is 0, 1, or 2.
- R 1 is hydrogen atom or an unsubstituted monovalent hydrocarbon group containing 1 to 10, and more preferably 1 to 6 carbon atoms such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group.
- Examples include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group; branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group; cyclic alkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, and propenyl group; aryl groups such as phenyl group and tolyl group; and aralkyl groups such as benzyl group and phenethyl group.
- the preferred are methyl group and ethyl group in view of the high utility of the resulting product and the relatively low boiling point of the resulting product.
- R 2 is hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group containing 1 to 10, and preferably 1 to 6 carbon atoms, and wherein the hydrocarbon group, when substituted, has a substituent from among alkoxy group and a group comprising a halogen atom, and wherein the hydrocarbon may be such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group.
- Examples include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group; branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group; cyclic alkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, and propenyl group; aryl groups such as phenyl group and tolyl group; and aralkyl groups such as benzyl group and phenethyl group.
- the preferred are hydrogen atom and methyl group.
- the monovalent hydrocarbon groups of R 2 may have some or all of their hydrogen atoms respectively substituted with a substituent.
- substituents include alkoxy groups such as methoxy group, ethoxy group, and (iso)propoxy group, groups comprising a halogen atom such as fluorine atom, chlorine atom, bromine atom, or iodine atom, and where the substituents may be used alone or in combination of two or more.
- R 3 and R 4 are respectively a straight chain or branched divalent hydrocarbon group containing 3 to 10, and preferably 3 to 6 carbon atoms.
- exemplary such groups include alkylene groups such as trimethylene group, tetramethylene group, hexamethylene group, and isobutylene group, and the preferred is trimethylene group in view of the availability of the starting material.
- R 4 may contain a heteroatom such as oxygen atom, nitrogen atom, or sulfur atom.
- R 5 and R 6 are respectively a monovalent hydrocarbon group containing 1 to 10, preferably 1 to 6, and more preferably 1 to 3 carbon atoms such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group.
- Exemplary such groups include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group, branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group, cyclic alkyl groups such as cyclopentyl group and cyclohexyl group, alkenyl groups such as vinyl group, allyl group, and propenyl group, aryl groups such as phenyl group and tolyl group, and aralkyl groups such as benzyl group and phenethyl group.
- the preferred are methyl group and ethyl group in view of the relatively low boiling point of the intended resulting compound.
- the distance between the nitrogen atom and each of the two alkoxysilyl moieties is preferably different, and this distance is longer than conventional compounds. Accordingly, a monolayer of the bisalkoxysilane compound represented by the general formula (1) provided by the present invention will be formed when the compound is used as a coating additive, fiber treating agent, silane coupling agent, surface treating agent, or the like, and the merit of the alkoxysilyl moieties is highly likely to be fully realized when the compound is used for such application.
- Examples of the bisalkoxysilane compound represented by the general formula (1) include:
- the production method of the bisalkoxysilane compound represented by the general formula (1) of the present invention is, for example, a method wherein a diolefin compound represented by the following general formula (2): wherein R 1 and R 2 are as defined above, R 3' is a straight chain or branched divalent hydrocarbon group containing 1 to 8 carbon atoms, and R 4' is a straight chain or branched divalent hydrocarbon group containing 1 to 8 carbon atoms which may also contain a heteroatom is reacted with an organosilane compound represented by the following general formula (3): wherein R 5 and R 6 are respectively a monovalent hydrocarbon group containing 1 to 10 carbon atoms, and n is 0, 1, or 2 in the presence of a platinum catalyst.
- a diolefin compound represented by the following general formula (2) wherein R 1 and R 2 are as defined above, R 3' is a straight chain or branched divalent hydrocarbon group containing 1 to 8 carbon atoms, and R 4' is a straight chain or branche
- R 3' and R 4' are respectively a straight chain or branched divalent hydrocarbon group containing 1 to 8, and in particular, 1 to 4 carbon atoms.
- exemplary such groups include alkylene groups such as methylene group, ethylene group, trimethylene group, tetramethylene group, hexamethylene group, and isobutylene group, and the preferred is methylene group in view of the availability of the starting material.
- R 4' may contain a heteroatom such as oxygen atom, nitrogen atom, or sulfur atom.
- R 1 , R 2 , R 5 , R 6 , and n are as described above.
- Exemplary diolefin compounds represented by the general formula (2) include bis(allyloxyethyl)amine, bis(allyloxyethyl)methylamine, bis(allyloxyethyl)ethylamine, bis(butenyloxyethyl)amine, bis(butenyloxyethyl)methylamine, bis(butenyloxyethyl)ethylamine, bis(pentenyloxyethyl)amine, bis(pentenyloxyethyl)methylamine, bis(pentenyloxyethyl)ethylamine, bis(hexenyloxyethyl)amine, bis(hexenyloxyethyl)methylamine, bis(hexenyloxyethyl)ethylamine, allyl-allyloxyethylamine, allyl-allyloxyethyl-methylamine, allyl-allyloxyethyl-ethylamine, butenyl-buteny
- organosilane compounds represented by the general formula (3) include trimethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, triethoxysilane, methyldiethoxysilane, and dimethylethoxysilane.
- the blend ratio of the diolefin compound represented by the general formula (2) and the organosilane compound represented by the general formula (3) is not particularly limited.
- the blend ratio is preferably in the range of 1.5 to 3.0 moles, and in particular, 1.8 to 2.2 moles of the compound represented by the general formula (3) in relation to 1 mole of the compound represented by the general formula (2) in view of the reactivity and the productivity.
- platinum catalysts used in the reaction as described above include chloroplatinic acid, alcohol solution of chloroplatinic acid, toluene or xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, tetrakistriphenylphosphine platinum, dichlorobistriphenylphosphine platinum, dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum, dichlorocyclooctadiene platinum, and platinum-active carbon.
- Amount of the platinum catalyst used is not particularly limited.
- the amount of the platinum catalyst is preferably in the range of 0.000001 to 0.01 mole, and in particular, 0.00001 to 0.001 mole in relation to 1 mole of the diolefin compound represented by the general formula (2) in view of the reactivity and the productivity.
- the reaction temperature in this reaction is not particularly limited, and the preferred temperature is 0 to 200°C, and in particular, 20 to 150°C.
- the reaction time is also not particularly limited, and the preferred time is 1 to 40 hours, and in particular, 1 to 20 hours.
- the reaction is preferably carried out in the reaction atmosphere of air or inert gas such as nitrogen or argon.
- reaction as described above may proceed either in the absence of a solvent or by using a solvent.
- solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene, ether solvents such as diethylether, tetrahydrofuran, and dioxane, ester solvents such as ethyl acetate and butyl acetate, aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, and N-methylpyrrolidone, chlorinated hydrocarbon solvents such as dichloromethane and chloroform, which may be used alone or in combination of two or more.
- hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene,
- the reaction as described above may progress with no particular use of additives. However, the reaction can be more quickly completed by adding particular additives.
- exemplary such additives include ammonium salts such as ammonium hydrogencarbonate, ammonium carbonate, ammonium acetate, and ammonium carbamate and carboxylic amides such as acetamide, formamide, and benzamide.
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Description
- The present invention relates to a bisalkoxysilane compound which is useful as a silane coupling agent, surface treating agent, resin additive, coating additive, adhesive, fiber treating agent, and the like. This invention also relates to its production method.
- Aminosilane compounds are useful for silane coupling agent, surface treating agent, resin additive, coating additive, and adhesive, and aminosilane compounds having hydroxyethyl group are particularly suitable for use in such application due to the high degree of freedom enabled by the presence of a spacer between the amino group and the silyl group. Examples of such aminosilane compound having the hydroxyethyl group include dimethylaminoethyloxypropyltrimethoxysilane and dimethylaminoethyloxypropylmethyldimethoxysilane, and these compounds have been described to be useful for use as the silane coupling agent, surface treating agent, resin additive, coating additive, and adhesive (Patent document 1: Korean Patent No.
10-1249352 2003/0196958 ). - All of these compounds have only one alkoxysilyl moiety per molecule, and sufficient coupling effect may not be realized at the alkoxysilyl group moiety when the compound is used as a silane coupling agent, surface treating agent, resin additive, coating additive, or adhesive.
-
- Patent Document 1: Korean Patent No.
10-1249352 - Patent Document 2: USSN
2003/0196958 . - N,N-Bis(Trimethysilylpropoxy-ethyl)-aniline is known from Polymer Preprints 2003, 44(1), 125, with CAS registry number 532930-34-0;
JP2010-100544 US2003/049486 discloses bis(trialkoxysilylpropyl)amines as coating additives. - The present invention has been completed in view of the situation as described above, and an object of the present invention is to provide a compound which is capable of exhibiting a higher effect than the compounds as described above when used as a silane coupling agent, coating additive, adhesive, or the like. Another object of the present invention is to provide a method for producing such compound.
- The inventors of the present invention conducted intensive study and found out that a novel bisalkoxysilane compound of the general formula (1) having two alkoxysilyl moieties in the molecule can be obtained by dihydrosilylation of a particular diolefin compound represented by the general formula (2) as described below, and since this bisalkoxysilane compound has two alkoxysilyl moieties in the molecule, the merit of the alkoxysilyl moiety will be fully realized when the compound is used as a coating additive, adhesive, silane coupling agent, or the like. The present invention has been completed on the basis of such findings.
- Accordingly, the present invention provides the bisalkoxysilane compound and its production method as described below.
- [1] A bisalkoxysilane compound represented by the following general formula (1):
- [2] A method for producing a bisalkoxysilane compound of [1] comprising the step of reacting a diolefin compound represented by the following general formula (2):
- The bisalkoxysilane compound provided by the present invention has two alkoxysilyl moieties in the molecule, and therefore, when the compound is used as a coating additive, adhesive, silane coupling agent, fiber treating agent, surface treating agent, resin additive, or the like, the merit of the alkoxysilyl moiety will be fully realized. Accordingly, properties of the resulting product will be improved by the addition of the compound, and the use of such compound is useful for such application.
-
-
FIG. 1 is a 1H-NMR spectrum of the 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine obtained in Example 1. -
FIG. 2 is an IR spectrum of the 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine obtained in Example 1. -
FIG. 3 is a 1H-NMR spectrum of the bis(trimethoxysilylpropyloxyethyl)methylamine obtained in Example 2. -
FIG. 4 is an IR spectrum of the bis(trimethoxysilylpropyloxyethyl)methylamine obtained in Example 2. - The bisalkoxysilane compound of the present invention is a compound represented by the following general formula (1):
- More specifically, R1 is hydrogen atom or an unsubstituted monovalent hydrocarbon group containing 1 to 10, and more preferably 1 to 6 carbon atoms such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group. Examples include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group; branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group; cyclic alkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, and propenyl group; aryl groups such as phenyl group and tolyl group; and aralkyl groups such as benzyl group and phenethyl group. The preferred are methyl group and ethyl group in view of the high utility of the resulting product and the relatively low boiling point of the resulting product.
- R2 is hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group containing 1 to 10, and preferably 1 to 6 carbon atoms, and wherein the hydrocarbon group, when substituted, has a substituent from among alkoxy group and a group comprising a halogen atom, and wherein the hydrocarbon may be such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group. Examples include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group; branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group; cyclic alkyl groups such as cyclopentyl group and cyclohexyl group; alkenyl groups such as vinyl group, allyl group, and propenyl group; aryl groups such as phenyl group and tolyl group; and aralkyl groups such as benzyl group and phenethyl group. In view of the availability of the starting material, the preferred are hydrogen atom and methyl group.
- The monovalent hydrocarbon groups of R2 may have some or all of their hydrogen atoms respectively substituted with a substituent. Exemplary substituents include alkoxy groups such as methoxy group, ethoxy group, and (iso)propoxy group, groups comprising a halogen atom such as fluorine atom, chlorine atom, bromine atom, or iodine atom, and where the substituents may be used alone or in combination of two or more.
- R3 and R4 are respectively a straight chain or branched divalent hydrocarbon group containing 3 to 10, and preferably 3 to 6 carbon atoms. Exemplary such groups include alkylene groups such as trimethylene group, tetramethylene group, hexamethylene group, and isobutylene group, and the preferred is trimethylene group in view of the availability of the starting material. R4 may contain a heteroatom such as oxygen atom, nitrogen atom, or sulfur atom.
- R5 and R6 are respectively a monovalent hydrocarbon group containing 1 to 10, preferably 1 to 6, and more preferably 1 to 3 carbon atoms such as straight chain, branched, or cyclic alkyl group, alkenyl group, aryl group, or aralkyl group. Exemplary such groups include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, and decyl group, branched alkyl groups such as isopropyl group, isobutyl group, and tert-butyl group, cyclic alkyl groups such as cyclopentyl group and cyclohexyl group, alkenyl groups such as vinyl group, allyl group, and propenyl group, aryl groups such as phenyl group and tolyl group, and aralkyl groups such as benzyl group and phenethyl group. The preferred are methyl group and ethyl group in view of the relatively low boiling point of the intended resulting compound.
- As described above, in the bisalkoxysilane compound represented by the general formula (1) having substituents, the distance between the nitrogen atom and each of the two alkoxysilyl moieties is preferably different, and this distance is longer than conventional compounds. Accordingly, a monolayer of the bisalkoxysilane compound represented by the general formula (1) provided by the present invention will be formed when the compound is used as a coating additive, fiber treating agent, silane coupling agent, surface treating agent, or the like, and the merit of the alkoxysilyl moieties is highly likely to be fully realized when the compound is used for such application.
- Examples of the bisalkoxysilane compound represented by the general formula (1) include:
- bis(trimethoxysilylpropyloxyethyl) amine,
- bis(methyldimethoxysilylpropyloxyethyl)amine,
- bis(dimethylmethoxysilylpropyloxyethyl)amine,
- bis(trimethoxysilylpropyloxyethyl)methylamine,
- bis(methyldimethoxysilylpropyloxyethyl)methylamine,
- bis(dimethylmethoxysilylpropyloxyethyl)methylamine,
- bis(trimethoxysilylpropyloxyethyl)ethylamine,
- bis(methyldimethoxysilylpropyloxyethyl)ethylamine,
- bis(dimethylmethoxysilylpropyloxyethyl)ethylamine,
- bis(triethoxysilylpropyloxyethyl)amine,
- bis(methyldiethoxysilylpropyloxyethyl)amine,
- bis(dimethylethoxysilylpropyloxyethyl)amine,
- bis(triethoxysilylpropyloxyethyl)methylamine,
- bis(methyldiethoxysilylpropyloxyethyl)methylamine,
- bis(dimethylethoxysilylpropyloxyethyl)methylamine,
- bis(triethoxysilylpropyloxyethyl)ethylamine,
- bis(methyldiethoxysilylpropyloxyethyl)ethylamine,
- bis(dimethylethoxysilylpropyloxyethyl)ethylamine,
- bis(trimethoxysilylbutyloxyethyl)amine,
- bis(methyldimethoxysilylbutyloxyethyl)amine,
- bis(dimethylmethoxysilylbutyloxyethyl)amine,
- bis(trimethoxysilylbutyloxyethyl)methylamine,
- bis(methyldimethoxysilylbutyloxyethyl)methylamine,
- bis(dimethylmethoxysilylbutyloxyethyl)methylamine,
- bis(trimethoxysilylbutyloxyethyl)ethylamine,
- bis(methyldimethoxysilylbutyloxyethyl)ethylamine,
- bis(dimethylmethoxysilylbutyloxyethyl)ethylamine,
- bis(triethoxysilylbutyloxyethyl)amine,
- bis(methyldiethoxysilylbutyloxyethyl)amine,
- bis(dimethylethoxysilylbutyloxyethyl)amine,
- bis(triethoxysilylbutyloxyethyl)methylamine,
- bis(methyldiethoxysilylbutyloxyethyl)methylamine,
- bis(dimethylethoxysilylbutyloxyethyl)methylamine,
- bis(triethoxysilylbutyloxyethyl)ethylamine,
- bis(methyldiethoxysilylbutyloxyethyl)ethylamine,
- bis(dimethylethoxysilylbutyloxyethyl)ethylamine,
- bis(trimethoxysilylpentyloxyethyl)amine,
- bis(methyldimethoxysilylpentyloxyethyl)amine,
- bis(dimethylmethoxysilylpentyloxyethyl)amine,
- bis(trimethoxysilylpentyloxyethyl)methylamine,
- bis(methyldimethoxysilylpentyloxyethyl)methylamine,
- bis(dimethylmethoxysilylpentyloxyethyl)methylamine,
- bis(trimethoxysilylpentyloxyethyl)ethylamine,
- bis(methyldimethoxysilylpentyloxyethyl)ethylamine,
- bis(dimethylmethoxysilylpentyloxyethyl)ethylamine,
- bis(triethoxysilylpentyloxyethyl)amine,
- bis(methyldiethoxysilylpentyloxyethyl)amine,
- bis(dimethylethoxysilylpentyloxyethyl)amine,
- bis(triethoxysilylpentyloxyethyl)methylamine,
- bis(methyldiethoxysilylpentyloxyethyl)methylamine,
- bis(dimethylethoxysilylpentyloxyethyl)methylamine,
- bis(triethoxysilylpentyloxyethyl)ethylamine,
- bis(methyldiethoxysilylpentyloxyethyl)ethylamine,
- bis(dimethylethoxysilylpentyloxyethyl)ethylamine,
- bis(trimethoxysilylhexyloxyethyl)amine,
- bis(methyldimethoxysilylhexyloxyethyl) amine,
- bis(dimethylmethoxysilylhexyloxyethyl)amine,
- bis(trimethoxysilylhexyloxyethyl)methylamine,
- bis(methyldimethoxysilylhexyloxyethyl)methylamine,
- bis(dimethylmethoxysilylhexyloxyethyl)methylamine,
- bis(trimethoxysilylhexyloxyethyl)ethylamine,
- bis(methyldimethoxysilylhexyloxyethyl)ethylamine,
- bis(dimethylmethoxysilylhexyloxyethyl)ethylamine,
- bis(triethoxysilylhexyloxyethyl)amine,
- bis(methyldiethoxysilylhexyloxyethyl)amine,
- bis(dimethylethoxysilylhexyloxyethyl)amine,
- bis(triethoxysilylhexyloxyethyl)methylamine,
- bis(methyldiethoxysilylhexyloxyethyl)methylamine,
- bis(dimethylethoxysilylhexyloxyethyl)methylamine,
- bis(triethoxysilylhexyloxyethyl)ethylamine,
- bis(methyldiethoxysilylhexyloxyethyl)ethylamine,
- bis(dimethylethoxysilylhexyloxyethyl)ethylamine,
- bis(2-methyl-3-oxy-6-trimethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-methyldimethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-dimethylmethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-trimethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-methyldimethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-dimethylmethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-trimethoxysilylhexyl)ethylamine,
- bis(2-methyl-3-oxy-6-methyldimethoxysilylhexyl)ethylamine,
- bis(2-methyl-3-oxy-6-dimethylmethoxysilylhexyl)ethylamine,
- bis(2-methyl-3-oxy-6-triethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-methyldiethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-dimethylethoxysilylhexyl)amine,
- bis(2-methyl-3-oxy-6-triethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-methyldiethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-dimethylethoxysilylhexyl)methylamine,
- bis(2-methyl-3-oxy-6-triethoxysilylhexyl)ethylamine,
- bis(2-methyl-3-oxy-6-methyldiethoxysilylhexyl)ethylamine,
- bis(2-methyl-3-oxy-6-dimethylethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-trimethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-methyldimethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-trimethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-methyldimethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-trimethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-methyldimethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-triethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-methyldiethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-dimethylethoxysilylhexyl)amine,
- bis(2-ethyl-3-oxy-6-triethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-methyldiethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-dimethylethoxysilylhexyl)methylamine,
- bis(2-ethyl-3-oxy-6-triethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-methyldiethoxysilylhexyl)ethylamine,
- bis(2-ethyl-3-oxy-6-dimethylethoxysilylhexyl)ethylamine,
- 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropylamine,
- 3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropylamine,
- 3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropylamine,
- 3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropylamine,
- 3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropylamine,
- 3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-methylamine,
- 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine,
- 3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-methylamine,
- 3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-methylamine,
- 3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-methylamine,
- 3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-methylamine,
- 3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-methylamine,
- 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-ethylamine,
- 3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-ethylamine,
- 3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-ethylamine,
- 3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-ethylamine,
- 3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-ethylamine,
- 3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-ethylamine,
- 3-oxy-7-trimethoxysilylheptyl-4'-trimethoxysilylbutyl-methylamine,
- 3-oxy-7-methyldimethoxysilylheptyl-4'-methyldimethoxysilylbutyl-methylamine,
- 3-oxy-7-dimethylmethoxysilylheptyl-4'-dimethylmethoxysilylbutyl-methylamine,
- 3-oxy-7-triethoxysilylheptyl-4'-triethoxysilylbutyl-methylamine,
- 3-oxy-7-methyldiethoxysilylheptyl-4'-methyldiethoxysilylbutyl-methylamine,
- 3-oxy-7-dimethylethoxysilylheptyl-4'-dimethylethoxysilylbutyl-methylamine,
- 3-oxy-7-trimethoxysilylheptyl-4'-trimethoxysilylbutyl-ethylamine,
- 3-oxy-7-methyldimethoxysilylheptyl-4'-methyldimethoxysilylbutyl-ethylamine,
- 3-oxy-7-dimethylmethoxysilylheptyl-4'-dimethylmethoxysilylbutyl-ethylamine,
- 3-oxy-7-triethoxysilylheptyl-4'-triethoxysilylbutyl-ethylamine,
- 3-oxy-7-methyldiethoxysilylheptyl-4'-methyldiethoxysilylbutyl-ethylamine,
- 3-oxy-7-dimethylethoxysilylheptyl-4'-dimethylethoxysilylbutyl-ethylamine,
- 3-oxy-8-trimethoxysilyloctyl-5'-trimethoxysilylpentyl-methylamine,
- 3-oxy-8-methyldimethoxysilyloctyl-5'-methyldimethoxysilylpentyl-methylamine,
- 3-oxy-8-dimethylmethoxysilyloctyl-5'-dimethylmethoxysilylpentyl-methylamine,
- 3-oxy-8-triethoxysilyloctyl-5'-triethoxysilylpentyl-methylamine,
- 3-oxy-8-methyldiethoxysilyloctyl-5'-methyldiethoxysilylpentyl-methylamine,
- 3-oxy-8-dimethylethoxysilyloctyl-5'-dimethylethoxysilylpentyl-methylamine,
- 3-oxy-8-trimethoxysilyloctyl-5'-trimethoxysilylpentyl-ethylamine,
- 3-oxy-8-methyldimethoxysilyloctyl-5'-methyldimethoxysilylpentyl-ethylamine,
- 3-oxy-8-dimethylmethoxysilyloctyl-5'-dimethylmethoxysilylpentyl-ethylamine,
- 3-oxy-8-triethoxysilyloctyl-5'-triethoxysilylpentyl-ethylamine,
- 3-oxy-8-methyldiethoxysilyloctyl-5'-methyldiethoxysilylpentyl-ethylamine,
- 3-oxy-8-dimethylethoxysilyloctyl-5'-dimethylethoxysilylpentyl-ethylamine,
- 3-oxy-9-trimethoxysilylnonyl-6'-trimethoxysilylhexyl-methylamine,
- 3-oxy-9-methyldimethoxysilylnonyl-6'-methyldimethoxysilylhexyl-methylamine,
- 3-oxy-9-dimethylmethoxysilylnonyl-6'-dimethylmethoxysilylhexyl-methylamine,
- 3-oxy-9-triethoxysilylnonyl-6'-triethoxysilylhexyl-methylamine,
- 3-oxy-9-methyldiethoxysilylnonyl-6'-methyldiethoxysilylhexyl-methylamine,
- 3-oxy-9-dimethylethoxysilylnonyl-6'-dimethylethoxysilylhexyl-methylamine,
- 3-oxy-9-trimethoxysilylnonyl-6'-trimethoxysilylhexyl-ethylamine,
- 3-oxy-9-methyldimethoxysilylnonyl-6'-methyldimethoxysilylhexyl-ethylamine,
- 3-oxy-9-dimethylmethoxysilylnonyl-6'-dimethylmethoxysilylhexyl-ethylamine,
- 3-oxy-9-triethoxysilylnonyl-6'-triethoxysilylhexyl-ethylamine,
- 3-oxy-9-methyldiethoxysilylnonyl-6'-methyldiethoxysilylhexyl-ethylamine,
- 3-oxy-9-dimethylethoxysilylnonyl-6'-dimethylethoxysilylhexyl-ethylamine,
- 2-methyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropylamine,
- 2-methyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropylamine,
- 2-methyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropylamine,
- 2-methyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropylamine,
- 2-methyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropylamine,
- 2-methyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropylamine,
- 2-methyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-methylamine,
- 2-methyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-ethylamine,
- 2-methyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-ethylamine,
- 2-methyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-ethylamine,
- 2-methyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-ethylamine,
- 2-methyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-ethylamine,
- 2-methyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-ethylamine,
- 2-ethyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropylamine,
- 2-ethyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-methylamine,
- 2-ethyl-3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-ethylamine,
- 2-ethyl-3-oxy-6-methyldimethoxysilylhexyl-3'-methyldimethoxysilylpropyl-ethylamine,
- 2-ethyl-3-oxy-6-dimethylmethoxysilylhexyl-3'-dimethylmethoxysilylpropyl-ethylamine,
- 2-ethyl-3-oxy-6-triethoxysilylhexyl-3'-triethoxysilylpropyl-ethylamine,
- 2-ethyl-3-oxy-6-methyldiethoxysilylhexyl-3'-methyldiethoxysilylpropyl-ethylamine, and
- 2-ethyl-3-oxy-6-dimethylethoxysilylhexyl-3'-dimethylethoxysilylpropyl-ethylamine.
- The production method of the bisalkoxysilane compound represented by the general formula (1) of the present invention is, for example, a method wherein a diolefin compound represented by the following general formula (2):
- In the formula (2), R3' and R4' are respectively a straight chain or branched divalent hydrocarbon group containing 1 to 8, and in particular, 1 to 4 carbon atoms. Exemplary such groups include alkylene groups such as methylene group, ethylene group, trimethylene group, tetramethylene group, hexamethylene group, and isobutylene group, and the preferred is methylene group in view of the availability of the starting material. R4' may contain a heteroatom such as oxygen atom, nitrogen atom, or sulfur atom. R1, R2, R5, R6, and n are as described above.
- Exemplary diolefin compounds represented by the general formula (2) include bis(allyloxyethyl)amine, bis(allyloxyethyl)methylamine, bis(allyloxyethyl)ethylamine, bis(butenyloxyethyl)amine, bis(butenyloxyethyl)methylamine, bis(butenyloxyethyl)ethylamine, bis(pentenyloxyethyl)amine, bis(pentenyloxyethyl)methylamine, bis(pentenyloxyethyl)ethylamine, bis(hexenyloxyethyl)amine, bis(hexenyloxyethyl)methylamine, bis(hexenyloxyethyl)ethylamine, allyl-allyloxyethylamine, allyl-allyloxyethyl-methylamine, allyl-allyloxyethyl-ethylamine, butenyl-butenyloxyethylamine, butenyl-butenyloxyethyl-methylamine, butenyl-butenyloxyethyl-ethylamine, pentenyl-pentenyloxyethylamine, pentenyl-pentenyloxyethyl-methylamine, pentenyl-pentenyloxyethyl-ethylamine, hexenyl-hexenyloxyethylamine, hexenyl-hexenyloxyethyl-methylamine, and hexenyl-hexenyloxyethyl-ethylamine.
- Exemplary organosilane compounds represented by the general formula (3) include trimethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, triethoxysilane, methyldiethoxysilane, and dimethylethoxysilane.
- The blend ratio of the diolefin compound represented by the general formula (2) and the organosilane compound represented by the general formula (3) is not particularly limited. The blend ratio, however, is preferably in the range of 1.5 to 3.0 moles, and in particular, 1.8 to 2.2 moles of the compound represented by the general formula (3) in relation to 1 mole of the compound represented by the general formula (2) in view of the reactivity and the productivity.
- Exemplary platinum catalysts used in the reaction as described above include chloroplatinic acid, alcohol solution of chloroplatinic acid, toluene or xylene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, tetrakistriphenylphosphine platinum, dichlorobistriphenylphosphine platinum, dichlorobisacetonitrile platinum, dichlorobisbenzonitrile platinum, dichlorocyclooctadiene platinum, and platinum-active carbon.
- Amount of the platinum catalyst used is not particularly limited. The amount of the platinum catalyst, however, is preferably in the range of 0.000001 to 0.01 mole, and in particular, 0.00001 to 0.001 mole in relation to 1 mole of the diolefin compound represented by the general formula (2) in view of the reactivity and the productivity.
- The reaction temperature in this reaction is not particularly limited, and the preferred temperature is 0 to 200°C, and in particular, 20 to 150°C. The reaction time is also not particularly limited, and the preferred time is 1 to 40 hours, and in particular, 1 to 20 hours. The reaction is preferably carried out in the reaction atmosphere of air or inert gas such as nitrogen or argon.
- It is to be noted that the reaction as described above may proceed either in the absence of a solvent or by using a solvent. Exemplary solvents used include hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene, ether solvents such as diethylether, tetrahydrofuran, and dioxane, ester solvents such as ethyl acetate and butyl acetate, aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, and N-methylpyrrolidone, chlorinated hydrocarbon solvents such as dichloromethane and chloroform, which may be used alone or in combination of two or more.
- The reaction as described above may progress with no particular use of additives. However, the reaction can be more quickly completed by adding particular additives. Exemplary such additives include ammonium salts such as ammonium hydrogencarbonate, ammonium carbonate, ammonium acetate, and ammonium carbamate and carboxylic amides such as acetamide, formamide, and benzamide.
- Next, the present invention is described in further detail by referring to the Example and Synthetic Example which by no means limit the scope of the present invention.
- In a flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 150.8 g (2.008 mole) of methylaminoethanol, 204.2 g (5.105 mole) of sodium hydroxide, 8.2 g (0.020 mole) of trioctylmethylammonium chloride, and 200 ml of tetrahydrofuran were placed, and the mixture was heated to 60°C. After stabilization of the inner temperature to 60°C, a mixture of 352 g (4.60 mole) of allyl chloride and 3.9 g of trioctylmethylammonium chloride was added dropwise in 2 hours, and the stirring was continued for 2 hours at the same temperature. After cooling to room temperature, 800 g of water was added, and the mixture was stirred at room temperature until the salt had been dissolved. After the separation, the organic layer was distilled off to obtain 213.8 g of a fraction of allyl-allyloxyethyl-methylamine having a boiling point of 95-96°C/6.0 kPa.
- In a flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 62.2 g (0.401 mole) of allyl-allyloxyethyl-methylamine synthesized in the Synthetic Example 1, 0.62 g of acetamide, and 0.53 g of a solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in toluene were placed and the mixture was heated to 60°C. After stabilization of the inner temperature to 60°C, 97.7 g (0.800 mole) of trimethoxysilane was added dropwise in 3 hours, and the stirring was continued for 4 hours at the same temperature. The reaction mixture was distilled to obtain 113.2 g of a fraction having a boiling point of 145-157°C/0.2 kPa.
- The thus obtained fraction was evaluated by mass spectrum, 1H-NMR spectrum, and IR spectrum.
Mass spectrum: m/z 399 250 208 121 91 72 1H-NMR spectrum (solvent, deuterochloroform): shown in the chart of FIG. 1 .IR spectrum: shown in the chart of FIG. 2 . - These results confirmed that the resulting compound was 3-oxy-6-trimethoxysilylhexyl-3'-trimethoxysilylpropyl-methylamine.
- In a flask equipped with a stirrer, a reflux condenser, a dropping funnel, and a thermometer, 40.0 g (0.201 mole) of bis(hydroxyethyloxyallyl)methylamine, 0.31 g of acetamide, and 0.27 g of a solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex in toluene were placed and the mixture was heated to 60°C. After stabilization of the inner temperature to 60°C, 49.1 g (0.402 mole) of trimethoxysilane was added dropwise in 2 hours, and the stirring was continued for 5 hours at the same temperature. The reaction mixture was distilled to obtain 58.6 g of a fraction having a boiling point of 157-170°C/0.4 kPa.
- The thus obtained fraction was evaluated by mass spectrum, 1H-NMR spectrum, and IR spectrum.
Mass spectrum: m/z 443 294 250 121 72 44 1H-NMR spectrum (solvent, deuterochloroform): shown in the chart of FIG. 3 .IR spectrum: shown in the chart of FIG. 4 . - These results confirmed that the resulting compound was bis(trimethoxysilylpropyloxyethyl)methylamine.
Claims (2)
- A bisalkoxysilane compound represented by the following general formula (1):
- A method for producing a bisalkoxysilane compound of claim 1 comprising the step of reacting a diolefin compound represented by the following general formula (2):
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